Hydrochloric Acid → 2-Hydroxymethyl-4-tritylmorpholine

HRID 440830Notes

Reaction equation

HRID 440830 reaction equation
C([O:4][CH2:5][CH:6]1[O:11][CH2:10][CH2:9][NH:8][CH2:7]1)=CC.Cl.[C:13]1([C:19]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)Cl)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])O.[Na+]>CC(C)=O.O.C(Cl)Cl.C(N(CC)CC)C>[OH:4][CH2:5][CH:6]1[O:11][CH2:10][CH2:9][N:8]([C:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:7]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6456Trityl chlorideHCID 516892Sodium BicarbonateHCID 541400752-(1-Propenyloxymethyl)morpholine

Product 1

HCID 544430302-Hydroxymethyl-4-tritylmorpholineYield 64.2%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolventHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

The crude 2-(1-propenyloxymethyl)morpholine (32.7 g) was dissolved in an acetone-water (9:1) mixed solvent containing 2.0N hydrochloric acid, followed by heating under reflux for 4 hours. After completion of the reaction, the solvent was evaporated to obtain a crude alcohol compound (41.8 g) as a pale yellow oily substance. Triethylamine (145 ml) was added dropwise to a methylene chloride solution (300 ml) of the crude alcohol compound (41.8 g) under ice-cooling, and triphenylchloromethane (41.5 g, 0.208 mol) was added thereto at the same temperature, followed by stirring for 2 hours. After completion of the reaction, a saturated aqueous solution of sodium hydrogencarbonate (150 ml) was added to the reaction mixture, and the mixture was extracted with chloroform. The extract was dried over magnesium sulfate, the solvent evaporated, and the residue recrystallized from methylene chloride-hexane to give 2-hydroxymethyl-4-tritylmorpholine (48.0 g).

Workup

  1. additionmixed solvent
  2. temperatureby heating
  3. temperatureunder reflux for 4 hours
  4. customAfter completion of the reaction
  5. customthe solvent was evaporated
  6. customto obtain a crude alcohol compound (41.8 g) as a pale yellow oily substance
  7. temperaturecooling
  8. customAfter completion of the reaction
  9. extractionthe mixture was extracted with chloroform
  10. dry with materialThe extract was dried over magnesium sulfate
  11. customthe solvent evaporated
  12. customthe residue recrystallized from methylene chloride-hexane

Sources & evidence

ORD record
ord-18b288cfe9b14ade8a0cd601334e9469
Source dataset
uspto-grants-1996_05
Patent number
US05521180

Reaction notes

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